


I know I don't know you (but I want you so bad)

by sarcastic_fina



Category: Arrow (TV 2012)
Genre: F/M
Language: English
Status: Completed
Published: 2014-01-27
Updated: 2014-01-27
Packaged: 2018-01-10 06:18:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 17,678
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1156148
Author URL: https://archiveofourown.org/users/sarcastic_fina/pseuds/sarcastic_fina
Summary: <blockquote class="userstuff">
              <p>(au) Oliver runs into his high school crush, Felicity Smoak, at a charity gala and he finally gets his chance to win the girl of his dreams.</p>
            </blockquote>





	I know I don't know you (but I want you so bad)

**Author's Note:**

> **Polyvore** : [outfit collection](http://www.polyvore.com/know_dont_you_but_want/collection?id=3297951), [lingerie](http://www.polyvore.com/cgi/thing?id=89913282)

Oliver wasn't a big fan of charity galas. Not because they weren't a worthy cause, but because they always bored him to tears. It was a constant merry-go round of fake smiles and hand shaking with people he didn't know, or particularly want to know. But as the son of a highly regarded Queen matriarch, he needed to pay his dues, even if he'd much rather be at Verdant, bent over his books, making sure everything was running smoothly.

He was casting his eyes around, searching for where his sister or mother might have wandered, when he spotted Tommy hurrying toward him. He was positively  _giddy_ as he reached Oliver, handing him a tumbler of bourbon with the goofiest grin Oliver had seen in ages.

"What?" he asked, staring at him, slightly suspicious. While Tommy had long settled down, it didn't stop him from occasionally pulling pranks to relive the glory days.

"You'll never guess who's here!"

"Everybody's here," Oliver reminded, waving a hand around meaningfully. "I think my mom invited half the state."

"No." He waved a hand dismissively. "Think more local. Think  _high school_ , blonde, awkward but in a cute way..."

Oliver went still, his eyes widening.

" _Yes!_ " Tommy cheered. "Your high school crush is here!" He laughed happily. "Do you remember how insanely awkward you were around her? That one time, you tried to ask her to the Valentine's dance and you just stood there, staring, until she walked away, completely confused." Tommy was clearly enjoying this; he was so amused there were tears in his eyes. "Oliver Queen, biggest flirt of our year, probably slept with half our graduating class, but froze up as soon as Felicity Smoak so much as breathed in your direction."

He shifted his feet, his eyes darting around nervously as he took a gulp from his drink. "She's here? You're not joking?"

"She's here." He nodded, grinning widely. "Yeah, I heard she's CEO of Smoak Industries now. Her dad retired a couple years ago."

"Makes sense," Oliver mused. "She was a tech genius."

He finally spotted her, standing just off to the side, nursing a glass of champagne. She was dressed in a sleeveless aquamarine gown with a paisley lace overlay, sheer above the sweetheart necklace. It hugged her body until it reached mid-thigh and then flared out to the floor, covering, what he was sure were, tall high heels, since she'd always been on the shorter side but now appeared almost statuesque.

"So? You gonna stare all night or finally make your move?" Tommy wondered, clapping him on the back encouragingly. He'd never quite understood what made Oliver freeze up every time he tried to talk Felicity, or why it always failed so spectacularly.

"Uh…" he trailed off, clearing his throat as he straightened out his tie uncomfortably.

"Don't tell me you're still nervous…" Tommy turned to him incredulously. "Ollie, it's been almost  _ten_  years!"

He frowned at his friend, disgruntled. "I know. I just… She's always kind of been… unattainable."

Tommy snorted. "Yeah, because you never managed to actually talk to her."

"I  _talked_ to her," he argued defensively.

Amused, his best friend shook his head. "Are you talking about that time at the dance…?"

Oliver's head cocked as he thought back to it. Grade eleven, the winter formal… God, he'd never live that down.

_December 10, 2001._

_Oliver never cared for dances; the few times he'd gone, he snuck out early with Tommy and a few willing girls for a better party of their own making. But he'd overheard Felicity talking to a few of her girlfriends that she would be going to the winter formal stag, her recent relationship with Taylor Jeffries fizzling out, again. Having had a crush on her since eighth grade, Oliver decided this might just be his chance._

_He bought a ticket, took his time getting ready, and turned down a number of invites both to the formal and to a private party after the dance. Tommy wished him luck and offered a final confidence boost in a full flask for him to take along with him so he wouldn't chicken out._

_Usually a guy who was happy to entertain any number of beautiful woman without breaking a sweat, Felicity was Oliver's one exception. For some reason, from the moment he'd seen her, he'd been intimidated. It wasn't completely surprised; she was the daughter of a prominent CEO and a genius if the fact that she'd been moved up a grade and was taking a number of advanced classes was anything to go by. Oliver, on the other hand, while also the son of a wealthy businessman, was not what most would call rocking the brains department too hard. Maybe it was too much partying or a lack of effort or maybe he just wasn't the genius his father was. He kept a solid B average, but a lot of that came from last-minute copying off of Tommy or getting one of the girls he was hooking up with at the time to do his homework for him. Sure, he was smart in some ways, but books wasn't one of them. Now women, that he could handle. He had no trouble charming a room full of women. Except one._

_In the two and a half years he'd known Felicity Smoak, he'd never once talked to her. They shared a few classes over the years and had a few mutual friends, but their circles in general were pretty different. He saw her at a few benefits too; their fathers might technically be business rivals, but they got along well enough that they went golfing together regularly. But, be it blessing or tragedy, their parents had never left them alone long enough to exchange hellos, let alone have a conversation. He was going to change that tonight._

_The formal was a little over the top in his opinion. Silver, blue, and white ran rampant. There was fake snow piled up over the edges of the auditorium and silver, glittery stars hung from the ceiling with disco balls intermixed. There was a table covered in refreshments, but one taste of the punch told him it was woefully unspiked. The music was loud, to the point that he would have to shout to be heard. He walked around the fringes, his eyes cast around for her familiar blonde ponytail. He saw a number of his own friends and stopped to chat, but turned down the offers for a dance from the girls that hung nearby. It wasn't like him, but he had a mission tonight, and that mission was a pretty blonde with the brightest blue eyes he'd ever seen._

_When he finally found her, his heart thumped in his chest. She was by the punch bowl, picking at a plate of desserts. She kept carefully clear of the peanut butter cookies; it was common knowledge from an incident in 9th grade that she was allergic to peanuts. He'd quit eating peanut butter soon after, illogically thinking that if he ever got a chance to kiss her he didn't want to send her in to anaphylactic shock. Tommy constantly bugged him about it, but thankfully didn't tell anybody else about his embarrassingly obvious crush._

_Clearing his throat, he checked his breath via his palm before walking over. He went through the different conversation starters in his head. He could ask her about her dad, about the homework assignment on Macbeth due on Monday, if she was having fun, the list was pretty much endless. Or he could just grin at her like he did most girls and ask her if she wanted to dance. Confidently, he stopped a few inches from her._

_She was wearing white; a pleated chiffon dress with a lace flower overlay. She had her hair pulled back in a French-braid, showing off the pearl earrings she wore._

_He opened his mouth to say something but nothing came out. Absolutely nothing. Not even a squeak._

_Seeming to notice someone nearby, she turned toward him, a brow raised curiously. She'd traded in her glasses for contacts, he noticed, and it only served to make her eyes pop even more than usual. Her makeup was light; she never was one for much makeup. Except for her lips, this time wearing a red wine color that matched her shoes and the beaded bangles on her wrist._

_She quirked her head, waiting for him to say something, anything, and he panicked. He tried grinning, but worried suddenly that it might look more like a grimace, and so tried to cover up how obviously ridiculous he probably looked by casually leaning against the table, except…_

_Her eyes darted down, brow furrowed, and then she took a step closer._

_His breath caught in his throat._

_"Your hand is in the punch bowl," she told him, just loud enough to be heard over the music but between them so nobody else would notice._

_He turned his head to find that yes, in his haste to look cool, he'd managed to stuff his hand into the punch bowl, soaking a good portion of his shirt sleeve._

_He was incredibly thankful for the dim lighting, because he was sure he'd never been so red in his life._

_Embarrassment was not something Oliver was all that familiar with. He could usually laugh off the worst of his behaviour, shrugging as if he didn't care, only this time he did._

_Felicity wasn't just a crush, she was, well, the girl of his dreams. And he knew how ridiculous that probably sounded; he hadn't even talked to her. But she was pretty and smart and when she laughed or smiled, his stomach did somersaults. He'd never felt like that about a girl. He_ liked  _girls; he frequently fucked girls; but he'd never been all that interested in anything more than that. He wanted to know her. Wanted to know what made her tick and what she thought about and what she liked or didn't like. He just wanted to listen to her talk for hours on end, until his ears finally gave up._

_Was that too damn much to ask?_

_Felicity reached for a stack of napkins nearby and pulled his arm out of the punchbowl. "Here," she said, stuffing most of the napkins into his dry hand._

_"Felicity!" someone shouted._

_She turned her head and Oliver followed her gaze to see Taylor Jeffries waving at her, and on his way directly to them. Great, now Taylor Jeffries was going to see how much of an idiot he was, wearing half the damn punch bowl on his arm._

_Felicity waved a hand at him and then looked back at Oliver. "We all make mistakes," she said, squeezing his forearm. "I won't tell if you don't."_

_With that, she hurried off, catching Taylor by the elbow and pulling him in the opposite direction._

_He watched her go, his heart plummeting to his stomach, all the while dripping punch all over the floor._

_That… was definitely not how he'd planned for this night to go._

_Sighing, he turned and walked off. He found a bathroom and cleaned himself up, but left the dance shortly after. Tommy was having a party and he planned to get so drunk he'd forget this ever happened._

"You showed up, completely miserable, and spent the whole night getting drunk, whining about punch and Taylor Jeffries."

Oliver felt a flush crawl up the back of his neck. "Yeah, I remember, thanks."

Tommy held his hands up in surrender. "Sorry."

"And anyway, that's not the time I was talking about." He glanced back toward Felicity and found her playing with her phone, an arm hugged around her waist.

"No? Maybe that time when you ran into her at the New Year's Party?"

Oliver frowned.

That… also wasn't one of his best moments.

_December 31, 2001_

_He was going to kiss her._

_Okay, so maybe talking to her first would be a better goal, but just as soon as he did that first part,_ then  _he was going to kiss her._

_On his way out of the house, his mother had told him to stay out of trouble, joking about the old adage 'whatever you're doing at midnight, you'll be doing for the rest of the year.' So he was going to talk to Felicity, woo her even, and come midnight, he was going to kiss her, and he was going to keep kissing her for the rest of the year._

_It was a good solid plan if it wasn't for one tiny flaw._

_She had a boyfriend._

_Taylor Jeffries was a douche._

_And Oliver wasn't even just saying that because he was the competition. It was a widely accepted fact that Taylor, who was captain of the basketball team and the mathletes, was an asshole. Sure, he had a lot of friends, was an A student, and was kind of handsome in that geeky jock kind of way, but his personality was total shit. Or it probably was. Oliver hadn't actually spent much time around him, being that he'd never joined a sports team and only knew of the mathletes because Felicity joined and they went to the state championships last year._

_So okay, fine, maybe he_ was  _only saying that because Jeffries was the competition. But Tommy agreed with him!_

_"Oh yeah, Taylor's a total dick," Tommy assured. "I mean, I'm pretty sure he volunteers at a soup kitchen and saves puppies from fires, but who knows, it's probably just for show."_

_Oliver rolled his eyes. "Nobody is that good. He's gotta have a flaw."_

_"Yeah, it would be dating your crush."_

_"And frequently breaking up with her!" Oliver pointed at him. "That's gotta count for something."_

_"Bad taste?" he wondered. "Or maybe he can feel you glaring at him and he's starting to catch on that it has to do with his girlfriend."_

_"See, that makes him selfish. If he really loved her, he'd stick around."_

_Tommy snorted. "I think you're grasping at straws."_

_"Well, I think I need another beer." Standing from the couch, he shuffled off to the kitchen for a refill, stopping at the keg to fill his blue cup._

_While waiting, he stared at the floor, his mind wandering. He frowned when he saw a pair of brown loafers appear. He snorted. Loafers had to be the most pretentious shoe ever. He followed them up to a pair of dark brown slacks, but as soon as he saw the tweed jacket he knew exactly who he was about to see. Taylor Jeffries was waiting, a red cup in hand. He was a big fan of his tweed jacket and bow tie, since he seemed to wear them often. Looked like the new year wasn't going to be any different._

_He offered a friendly grin when Oliver met his eyes before he turned his head to scan the crowd curiously._

_Oliver stared at him a long second before turning back to the keg and continuing to pour his fill. "You're, uh, Taylor, right?" he asked, feigning uncertainty._

_Taylor looked back. "Yeah, Taylor Jeffries." He pointed a finger. "Oliver Queen, right?"_

_"Yeah." He nodded, glancing back down at his cup. "You havin' a good night?"_

_"Sure." He shrugged. "I don't come to a lot of these things. Busy schedule, you know?"_

_He hummed. "Yeah, well, there's always time for a party, I say."_

_Taylor shrugged. "To each their own."_

_Finished filling his cup, he stepped back to let Taylor take over, but lingered. "Hey, aren't you dating, uh, what's her name… Felicity…? Smoak," he clarified._

_Taylor nodded. "Mm-hmm. Yeah, she's here with me tonight. Somewhere." He shrugged. "If she found Kelsey, I'm not gonna see her until next year."_

_Oliver offered a faint laugh at the poor excuse for a joke. "You and Felicity been together long?" he wondered, taking a drag from his beer._

_"I guess, sure. About two years."_

_"Two years, wow."_

_"She's one of those girls, y'know. Long term commitment." He shrugged. "I'm not complaining. She's smart, keeps me on my toes." He half-smiled. "Who knows, ten years down the line, she might be Felicity Jeffries."_

_"Yeah…" Oliver chuckled awkwardly, a sour taste in his mouth. "Well, have a good night." He raised his cup. "Happy New Year." With that, he turned on his heel to leave._

_When he found Tommy, he was busy, a brunette on one knee and a red-head on the other, his mouth buried at the brunette's neck while he stroked the hair of the red-head. He traded back and forth between them, grinning widely, while Oliver knocked back the rest of his beer. He found a tale covered in liquor bottles and filled his empty cup with the first thing he grabbed. While it sloshed into the cup, he took up another bottle and knocked back a long drag. Shaking his head at the bite that stung down his throat, he smacked his lips, picked up his cup of unknown and walked off. He needed to get drunk, and fast._

_An hour later, Oliver wasn't just drunk, he was completely pissed out of his tree. He was pretty sure this would be another of the nights he woke up on the lawn with the sprinkler shooting him in the face. Wouldn't be the first, or last, time._

_He stumbled through the house, searching for Tommy, who had his car keys stashed somewhere. The room was tilting and people were blurring. The music was loud enough that it made his head feel like it was throbbing along with it. He thought he saw a familiar face near the kitchen and made his way in that direction, but when he got there, he found only one person sitting on the counter, nursing a blue cup._

_She was dressed in red satin, a sinfully beautiful dress that huffed her body nicely. Her legs were crossed at the ankle, tall black heels with interlocking straps making a pattern over the front of her feet. He stared at her a long moment, wondering if he was drooling. God, she was beautiful._

_Felicity's head raised abruptly and he wondered if he'd said that out loud. It was common knowledge that his filter was completely broken when he drank._

_She eyed him curiously before raising her cup for a sip, her gold bangles sliding down her wrist._

_He walked toward her in a fashion he hoped seemed coordinated. He was going to ask her how she was liking the party, or maybe where her friend Kelsey was, or if she had any New Year's resolutions. And then he'd say something flirty like, "If you want a new boyfriend for next year, I'd be happy to apply."_

_He opened his mouth to start, but found himself distracted by how pretty she was. Her hair was up in a slicked back ponytail, falling pin straight down her back. She was tugging on one of her ears, rolling the earring nervously. And her lips, a liquid red, were only hindered by her teeth pressing down into the bottom. She was wearing her glasses this time, square frames with a slight upturn near the corners, not quite cat's eyes but similar. They were cute, just like her._

_Introductions, his alcohol sodden brain told him._

_He reached a hand out as if to shake hers, but just as he was about to tell her his name, his stomach lurched._

_And that was how he found himself with his hands braced on the counter, bent forward, puking on her shoes._

_He was never going to live this down._

_A soft sigh could be heard from above, and he swore the tears biting at his eyes were just from vomiting so violently and not the insane embarrassment of having just done what he did in front of her, of all people._

_"Well, now I've got an excuse to get out of these shoes," she muttered._

_He stumbled back, wiping a hand over his mouth. Just as he was about to apologize, his stomach twisted up again and he found himself leaning over the sink, puking so hard his whole body shook with it. It'd be a few minutes before he looked up and Felicity was long gone. There was a bottle of water waiting for him though, so he thought she might've taken a little pity on him._

_Groaning, he rested his forehead down on his arm and wondered if he'd ever catch a break._

Oliver closed his eyes and let out a long, pitiful sigh. "You think she remembers that?"

"Well, you definitely left a mark…" Tommy mused, brow arched and a highly  _un_ sympathetic smile playing over his mouth.

He glared at him. "I did manage one conversation with her without making an idiot of myself, you know."

Tommy tipped his head to the side thoughtfully. "Enlighten me, 'cause it's not ringing a bell…"

"It was one of your house parties…"

_Summer, 2002_

_Tommy's parties were always the loudest, biggest event in town. Oliver didn't think he knew even half the people currently invading Merlyn Manor, but that didn't stop more from pouring inside. He spotted Tommy across the room, dancing in the middle of a group of girls, eager for the host's attention. Seeing Oliver, he raised his beer and waved him over to join him, but Oliver shook his head, giving him a thumb's up to keep enjoying himself._

_Oliver needed a breather. It wasn't that he wasn't having a good time. He was. He was just feeling a little… what was that word Raisa always used on rainy days? Melancholy? By this time next year, he'd be a high school graduate and on his way to whatever Ivy League school his dad decided was good enough for the Queen progeny. It felt like all the good times were coming to an end and he wasn't looking forward to that. He wasn't looking forward to college either. If he had a choice, he'd just continue on with life just as it was. Right here, in the middle of a party, a king on his throne._

_He stepped outside, breathing in deep. The sun had long set, leaving the sky a blanket of black with only the stars to wink back at him. He walked down the stairs of the porch to the huge expanse of backyard. Tommy's one and only rule was that nobody go into the backyard during a party, mostly because his mother's garden was there and he refused to let anybody trample all over it. So when Oliver saw a figure in the gazebo on the chair swing, he walked over to tell them to move on. He assumed it was probably some couple, taking advantage of the space and quiet to hook up._

_The closer he got, however, the more obvious it was that the person was alone._

_He stumbled on the stone path when he recognized her._

_Felicity had her hair down, thick curls falling around her shoulders. Her arms were crossed over her chest, whether from comfort or to keep the cold at bay he wasn't sure. The blue top she was wearing had spaghetti straps, the fabric thin and floaty. She had her legs crossed, a strappy red heel bouncing, while her head was leaned back, staring up at the sky._

_He was already going through options for how to approach her when he noticed her hand reach up, gold and blue bangles sliding down her forearm while she swiped under her eye as a tear slipped out the corner._

_He paused. Crying women were not his forte. He could admit that occasionally he'd used it to his advantage, convincing a girl who was fighting with her boyfriend to get back at him by hooking up with someone else, namely him. But as he looked at Felicity, he didn't imagine she'd fall for that, nor was that what he really wanted. Not that he'd turn her down if she offered, but over the last few years, he'd realized screwing around with her wasn't the limit of what he wanted._

_Taking a deep breath, he walked forward, stuffing his hands in the pockets of his jeans. "Hey," he said cautiously._

_Flinching, she sat up abruptly, wiping at her face. "Uh, hi…" She sniffled quickly, letting her hair fall to cover her face as she hurried to hide the evidence._

_"Are… you okay?" he wondered, brows hiked._

_"Yeah, uh…" She swiped under her nose and pushed her hair back. "Yeah, fine. Thanks for asking." She stood from the swing, smoothing out her jeans. "Sorry, I know Tommy doesn't like people coming in the backyard, I just… needed some air."_

_Oliver shrugged. "No, it's fine…" He reached up to run a hand back through his hair. "You, uh, sure you're all right?"_

_She glanced at him and then away. "Yeah, I'm just…" She shrugged. "I broke up with my boyfriend." Rolling her eyes at herself, she let out a snort. "Which is dumb, right? I mean, I shouldn't be the one crying, he shoulder. Not—Not that he should be sobbing because he lost me or anything. I just mean because I broke up with him, not the other way around, so there's kind of like an expectation that I shouldn't be upset. But, well, we were together for a while and I know we broke up a lot, but this time it's kind of… permanent, so… I don't know. I thought I'd be okay with it. I know it's the right thing to do, but… Two and a half years is a long time and I know we don't really work together but I'll… miss him, I guess."_

_Oliver nodded. "Makes sense to me."_

_She looked up at him, smiling faintly. "Glad it's not just me then…"_

_He walked a little closer. "So, what… Why'd you break up?" He paused, glancing away. "Unless that's too personal." He waved a hand. "You don't have to answer that."_

_"No, it's fine. I…" She frowned. "I loved Taylor. He was… smart and handsome and he always made me feel loved. But…" She huffed out a sigh and plopped back down on the chair swing. "I kind of felt like we were in this weird rut. Like we were only together because we were used to each other. So all that good stuff, that passion, just kind of drained away." She tucked her hair behind her ear. "In the beginning, we'd see each other and my heart would race and my hands would get sweaty and I'd feel like such a dork every time I tried to talk to him… Have you ever felt like that?"_

_He nodded, wiping his palms on his jeans. "Yeah."_

_"Yeah, well, it was like that, but then… I don't know. I guess that part just kind of fades eventually. I mean, you get used to each other, right? So that makes sense. And relationships aren't built solely on sex and attraction. There's gotta be substance there too, right? Not that there isn't that with him. Because he's smart. Insanely smart. A little too much sometimes, so he can come off like kind of a pretentious jerk, but… That's whatever. We all have flaws. The real problem was that the passion went away pretty quick, but by that time we were friends and we were comfortable with each other and I still liked him, you know? But I just… I mean, I'm sixteen. I should want passion, right? I should want adventure and excitement and I shouldn't feel like I'm sixty and settling. So… I decided enough was enough and we should stop pushing something that obviously wasn't working for us."_

_He stared at her, watching her hands move around animatedly._

_"Do you think that's selfish?" she wondered, chewing her lip. "I mean, he was happy, he said so, but… I wasn't. I was… bored." Her nose wrinkled._

_His mouth twitched with a smile and he ducked his head to hide it. "I don't think that's selfish," he told her. "You should have passion."_

_She stared down at him, red lips curled up in a half-grin. "Yeah!" she agreed. "Besides, Taylor will bounce back. Half the girls in my year flirt with him. He's probably getting sympathy sex right now…" Her eyes narrowed thoughtfully as she stared at the house. "That should probably bother me more than it does."_

_A little alarm went off in his head. A sign that this was his in. If this was any other girl, this would be the time to say, "You could be having sympathy sex right now too," or "I can show you passion."_

_Instead, he said, "Are you cold?"_

_Her eyes fell to meet his again. "Oh." She rubbed her arms. "A little. It's weird, right? How cold it gets at night, even in summer?" She shook her head. "Kelsey told me to bring a jacket, but it was nice out when I was getting ready, so I figured I'd be fine. Then again I wasn't planning on going outside at all, or breaking up with Taylor_ at  _the party. But, well, then he made this really terrible joke, like the kind your dad makes and thinks is so funny, and the next thing I know I'm telling him I think we should break up…" She shook her head. "So we found a room and talked a bit and well, it's over." She rolled her eyes. "Not that you really wanted to know… any of that. You were just being polite and probably looking for a quiet place, and now I've ruined that by babbling, which I will stop doing in 3… 2..."_

_He grinned at her before sitting back and shrugging off his leather jacket. He held it out to her and she glanced at it briefly, raising a brow. "You don't have to…"_

_He wiggled the jacket and she let out a sigh, taking it from his outstretched hand and pulling it on. It was large on her small figure, swamping her, but it only made her look cuter. There was something incredibly attractive about her being in his clothes. Even if it was just a jacket._

_She hugged it closed over her chest and faced him, legs crossed once more. "So, I didn't ask what you're doing out here…"_

_He shrugged. "Just needed a minute away from the party."_

_"Too loud?"_

_He shook his head. "Just been thinking… One year left to graduation and then everything changes."_

_She tipped her head, staring at him curiously. "Big plans after grad?"_

_He frowned. "Harvard, Brown, Yale, whatever my dad picks."_

_Her brows hiked. "Big names."_

_"Only the best for a Queen," he muttered._

_"You don't sound too excited about that..."_

_He ran a hand through his hair as he blew out a sigh. "Never really saw myself going to college… Not something I really wanted for myself."_

_"So why go?" she wondered, her voice devoid of the judgement he always expected._

_He looked at her, her sincere eyes meeting his. "It's expected," he answered simply. "Dad's a business mogul; I'm supposed to follow in those shoes."_

_"Sure, if you want to." She shook her head. "It's not written in stone. As clichéd as it might sound, we all set our own paths, if we want to, that is. You can either follow the status quo and do what's expected or you can forge your own path and do what makes you happy." She rolled her eyes, letting out a light chuckle. "And there is Felicity Smoak's words of wisdom, not that they'll suddenly make everything clearer."_

_His mouth turned up a little in amusement. "You know, no one's ever said that to me, actually."_

_Her eyebrow quirked. "What? That you can say no and go your own way?"_

_He nodded. "Usually if I say I'm not really into it, they tell me that I'm just too young to realize it's what I need. That I'll get used to it or I'll like it when I get my first pay check. But… I don't know. Maybe it's because I've never really had to make any big decisions for myself, I've always had things just… given to me. But I don't want to be my dad. I don't want the big office or the business degree or the CEO title. I just want this. I want to be free and happy and have all my friends around me."_

_"Do you want the perpetual party or the feeling you get when you're there?" she wondered._

_His brow furrowed. "What's the difference?"_

_"That feeling comes from other things, too. Just because you always feel it when you're the life of the party doesn't mean you won't enjoy it doing something else. Maybe you just haven't figured out where you fit yet, but when you do, you can be happy." She leaned back in her seat. "But just as a general piece of advice, doing something because other's want you to or because you think you should, that never turns out well for you. You'll just end up miserable. Rich, sure, but miserable. Take it from the daughter of a very cranky CEO who never wanted to inherit the company from his father." She offered a light smile before tipping her head back and looking up at the stars once more._

_He stared at her profile a while; she was even prettier than he thought. He could see freckles on the bridge of her nose and his stomach did that awful flip it always did. A wistful sigh left him, making him clear his throat as an embarrassed flush flared across the back of his neck. He opened his mouth to say something, anything, to keep her talking to him, but a voice interrupted._

_"Felicity! Where the hell have you been?" Kelsey Daniels stumbled into view. "I've been looking for you everywhere. I heard about you and Taylor. Are you okay?"_

_Felicity smiled up at him and stood from the swing. "Yeah, I'm actually feeling pretty good." She accepted Kelsey's hug, squeezing her lightly._

_"Come on. Let's get you a drink and a rebound."_

_Felicity laughed, shaking her head. "You know what? I think I'm gonna swear of guys for a while and just focus on me. It's my last year, what's the point in having a boyfriend if we're just going to split up when I have to move for college?"_

_"I didn't say you needed a boyfriend. I'm saying let's get you laid. Huge difference!" Hooking her arm around Felicity's waist, she drew her back in the direction of the house. "So on a scale of one to I would totally bang him, where is Carter Bowen, because he's been checking you out for weeks!"_

_Oliver flinched._

_"Try negative five. I don't care how pretty that face is, he has to the most pretentious jerk I've ever met."_

_And then he grinned._

_Sitting back in the swing, he turned his own head up to see the sky. So maybe he hadn't won the girl, and it looked like she wasn't interested in anything long term, but at least Carter Bowen wouldn't be getting his crush on top of everything else._

_As a shooting star flared across the sky, he sent up a hope that one day he might have a real chance with the girl of his dreams._

"Wait, why didn't I ever hear about this?" Tommy wondered.

Oliver shrugged. "I told you the next day, but you were sleeping off a massive hangover and told me to stop rubbing my happiness in your face when your mouth tasted like dirty socks."

"Okay, well, here's your chance to show her that her advice turned your life around." Tommy shoved his shoulder. "Go, tell her you opened your own chain of night clubs and are one of the most successful men in Starling City." He brightened. "Ooh, tell her you were #1 on Starling's Sexiest Bachelors list last year." He clapped his hands. "Tell her about the book you're writing!"

"I don't think she wants a laundry list of my accomplishments," he muttered, eyeing her across the room, shaking hands with a senator. He paused. "Would she?"

"I wouldn't start with that. But, then again, from what I hear you tend to make a fool of yourself around her, so maybe start with something small, like, 'Hey, I'm Oliver, you might not remember me, but I had a massive crush on you and frequently did really embarrassing things in an effort to get your attention.'"

Oliver frowned as he turned to find his sister smirking at him. "Thea…" he sighed.

"Remember that party you had where you jumped off the roof into the pool because you thought it would impress her?" she asked, laughing.

"And broke your arm," Tommy added, raising his glass in cheers.

"Or when you tried to make her jealous by dating one of her friends, but the girl you picked was  _also_ totally crushing on her and was actually dating you to see if she would get jealous…"

"Oh my god, I forgot about that!" Tommy exclaimed, throwing his head back. "What was her name?" He snapped his fingers. "Cassie Something. She talked about Felicity more than you did." He slapped his shoulder. "You remember when you two were fooling around and she told you to call her Felicity."

Oliver dragged a hand down his face. "Okay, that was a mistake, obviously. Cassie was a little… obsessed."

Thea's brows hiked. "Obsessed is being kind. I heard she was locked up for stalking some guy she thought was her soul mate…"

"Well, hopefully she's getting help." He frowned. "Can we please stop talking about this?"

"No way. Are you kidding?" She scoffed at him. "This is the only girl you've ever been interested in longer than the time it takes to get your pants off!"

"I was with Laurel for like, three years," he argued.

"Yes, but she married your best friend, so I hardly think that counts," Thea dismissed.

Tommy shrugged. "I don't know what the logic in that is, but it works for me."

Oliver rolled his eyes. "The point remains that this was all ten years ago. She probably doesn't remember me. And I've moved on."

"Have you? Because you've barely taken your eyes off her…" Thea told him, looking smug.

"Only because we're talking about her. I'd prefer if her bodyguard, who looks like two men rolled into one, didn't overhear this conversation and think that we were creepy Cassie-like stalkers," he muttered.

"Well, I think you should go talk to her. She's been entertaining old money all night. She probably needs a breather." Thea wiggled her eyebrows. "And it's about time you made me an aunt. You're getting old, Ollie. It's time to settle down."

He choked on air and passed a glare at her. "Not so loud, mom might hear you."

"Mom might hear what?" Moira's voice interrupted.

Oliver flinched, turning to face her. "Mom," he said, leaning in to kiss her cheek. "Nothing. Thea was just telling Tommy here he should pop out a few kids so she can babysit."

"He's not the only one," Moira answered, half-smiling.

He rolled his eyes, mouth settling in a frown. "Where's Walter?" he wondered, casting his eyes around curiously, hoping to change the subject.

"I'm sure he's around somewhere." She raised her champagne class in askance and wondered, "So? Have you gathered enough courage to speak to Miss Smoak yet?"

He sighed, his head falling back. "Not you too."

She smiled at him teasingly. "Honey, it's not like you were being very subtle."

"When? Now or all through high school?" Tommy piped up, amused.

"Both times." Her brows hiked as she turned to Oliver and readjusted his tie. "Frankly, I'm amazed she doesn't have a date on her arm. She's one of the youngest CEOs here and her company is flourishing. Not to mention how smart and beautiful she is…" She eyed him, a certain weight to her gaze. "It looks like your taste is improving."

"Technically I've liked her since I was fourteen, so my taste has always been impeccable."

Humming disagreeably, she said, "I can count on both hands how many girlfriends you've had that I wished you hadn't, starting with that Cassandra Smith girl that stole a police car last year and led the SCPD on a high speed chase for four hours."

"In my defense, I dated her when she was sixteen and a little less crazy…"

"Emphasis on 'a little,'" Thea mocked.

"None of this is encouraging me to talk to her," Oliver complained.

"I can introduce you," Moira offered, brightening up. "Oh, I'd love to. She's such a delightful woman. We had a lovely conversation earlier about her mother. We went to school together, in fact. She's just like her. Rambles a bit, but in a sweet way."

"You have your mom's approval. Do you know how huge this is? You are digging a grave here, buddy. Jump in or start running," Tommy told him.

"Who are we talking about?" Laurel wondered, coming around to hook her arm in Tommy's elbow.

"Oliver's high school crush is here," Thea told her, not to subtly pointing in the direction of Felicity, who was having a word with her bodyguard.

"She's probably asking him if he's noticed the large collection of people all talking about her so he can sneak her out the back," Oliver sighed, pinching the bridge of his nose.

"She's pretty," Laurel commented, looking back to smile at Oliver. "High school crush, huh?"

"You should've seen him," Tommy crowed. "The first time he saw her, we were sitting in the cafeteria and he was so distracted, he walked into someone. Their tray flipped and he was  _covered_ in creamed corn. I've never laughed so hard in my life." He chuckled deeply at the memory.

"Oh, that's terrible," Laurel sympathized, wincing.

"He didn't have spare clothes, so I had to drive to the school and drop some off," Moira mentioned, eyes turned up thoughtfully. "I've never seen him so embarrassed before."

"Well, it only got worse," Tommy mused.

Oliver glared at all of them. "I was nervous. She was the first girl I actually liked."

"How old were you?" Laurel wondered.

"Fourteen when it started. I haven't seen her since graduation." He shifted his feet, glancing past Laurel's shoulder to find Felicity was no longer where he'd last seen her.

His eyes started darted around, searching for her in the crowds of people. Disappointment settled heavily in his gut. The first time he'd seen her in ten years and he'd already lost his chance. He frowned, hands balling up into fists. Great. As much as he'd been worried about how he might approach her, feeling just like the nervous teenager he'd once been, he had still held out hope that tonight might be different. As soon as Tommy pointed her out, he'd felt his heart swoop. She was even more stunning than she was when he'd last seen her. And if it took him this long to see her again, what were the chances he'd be seeing her again anytime soon?

"Excuse me?"

His heart stopped for a second, his eyes wide, and, very slowly, he turned around.

Felicity Smoak was standing in front of him, her hands clasped together, showing off the gold bracelet she wore in a pretty leaf design and her bright purple finger nails.

"Mrs. Queen, I just wanted to thank you for inviting me tonight. Things have been hectic lately with Smoak Industries, so it was nice to come out and mingle." She smiled warmly. "And I really enjoyed our conversation about my mother. It's been difficult since she passed away, but your stories feel like I was connecting with her again."

"Of course!" Moira smiled down at her, reaching for Felicity's hands and squeezing gently. With a wink, she added, "I'm so happy you could come out, dear. If anyone knows how busy life as a CEO can get, it's me." Releasing one of her hands, she turned, "Oh, and while you're here, why don't I introduce you to my children." She motioned toward Thea, who happily moved to her side. "This is my daughter, Thea. She's finishing her last year in high school."

"Oh? Are you at Rosemary Academy?" Felicity wondered, brightening.

"Yeah!" She grinned, elbowing Oliver in the side. "Trying to live up to this one's legacy."

Moira stepped in once more. "Yes, and this is my son—"

"Oliver," Felicity said, looking up at him. "I haven't seen you since graduation."

He let out a breathless sigh. "Yeah, uh, you too." He winced, closing his eyes and giving his head a shake. "I mean, it's been a while. How are you?"

Her smile widened. "Busy, mostly." She shrugged. "Pays the bills."

"If I remember correctly, the paycheck shouldn't matter if you're happy."

"Having both helps… I'd love to catch up with you, but I was just heading out." She shrugged. "Much as I love events like this, it's hard to trust the buffets, and I'm starving."

"She's allergic to peanuts," Oliver informed the others absently. "Uh, if you're up to it, we could get dinner," he suggested, his heart beating loudly in his ears.

"Sure, I'd like that." She motioned behind her. "I'll just tell Digg that we're heading out. Unless you have a car you'd rather take."

"Uh, yes, I brought my own."

"Okay. Well, he probably wants to head home early anyway. Meet you outside?"

He nodded, biting his tongue so he wouldn't accidentally say anything stupid.

"Great." She turned back to Moira. "Thank you again. I look forward to lunch next Tuesday."

"Yes, me too!" Moira beamed at her.

"It was nice meeting you, Thea," Felicity offered. "Have a great night."

"Yeah, you too," Thea told her with a grin, looking between her and Oliver.

With one final wave, Felicity turned on her heel and made her way back toward the wall of muscle that was her bodyguard and driver.

Oliver stared after her, slightly agape, until Tommy's hand abruptly clapped his shoulder. "You just got a date with Felicity Smoak," he said, laughing in his excitement.

He turned to face him, feeling a little shell shocked. "She said yes."

"She said  _yes!_ " Tommy nodded.

His face fell as he blanched. "What if I screw up?"

"Can you really screw up worse than vomiting on her shoes?" Thea wondered.

Oliver glared at Tommy. "How much did you tell her?"

He shrugged. "It was a bonding moment. Little sisters appreciate having dirt on their brothers."

"Pretty sure best friends of  _said_ brother aren't supposed to be the one dishing out the dirt," Laurel reminded, dusting off his shoulder as she smiled up at her husband knowingly.

"I'd lie and say she plied me with alcohol but mostly I just like talking about the old days, before Oliver became an upstanding citizen."

"And I deeply appreciate that he has," Moira offered, squeezing her son's arm affectionately. "Don't worry so much. She's a perfectly nice girl who said yes for a  _reason_. You left an impression, if nothing else. So go with it and show her that you're more than the lovesick boy she remembers from high school."

He sighed. "I wasn't lovesick…"

The unconvinced faces looking back at him made him glower. "Okay. Thank you all for your  _incredible_ empathy and encouragement," he told them sarcastically before he straightened his tie and took a deep breath. "I'm going to go find my car and hope I don't embarrass myself in the meantime." With a farewell kiss to Thea's, Laurel's, and his mother's cheek, he clapped Tommy's shoulder and turned to leave.

"Good luck!" Thea called after him cheerfully.

He waved a thumb's up back at her and kept going. On the way, he barely restrained himself from knocking back a flute of champagne for courage. Just as he was nearing the door, however, Felicity's bodyguard stepped out of from what appeared to be the shadows near the cloakroom.

He'd never admit he jumped a little. "Uh, hi, it's Digg, right?" He held a hand out for him to shake.

"John Diggle," he answered, casting a dismissive glance down at Oliver's hand. "Miss Smoak's personal guard." He clasped his hands in front of her. "It's against my better judgement that she leave here with you, but she was adamant that she would be fine. I decided to make sure for myself."

"Okay." He offered a faint grin and nodded. "Is there something you wanted to ask? Or maybe I could have a criminal record check sent to you." He paused, his eyes turned up to the side. "Actually, maybe we should rain check on the record check. I was a… foolhardy teenager."

Digg didn't laugh or smile. He stared down at Oliver stoically. "I'm sure that's funny to you, and maybe under different circumstances I could see the humor. But I've been guarding Miss Smoak's life for six years and my one mistakes won't be at the hands of a trust fund baby out for kicks. Felicity is more than capable of choosing who she spends her personal time with, but if you've been drinking tonight and you plan on getting behind the wheel of a car that she's in, this is going to be a problem."

Oliver held his hands up in surrender. "I had a bourbon, an hour ago. I'm not buzzed. But if you're concerned, I'd be happy to take a cab."

Diggle hummed, still looking at him, a disgruntled frown marring his mouth. "Miss Smoak and I have always been plain with each other, so I'm going to be clear with you… That woman is a good person. I don't mean just as a business mogul or in a 'she donates to charity' kind of way. I mean, she's got a good heart. And when I signed on to be her guard, that wasn't just to protect her in the event that there was an attempt on her life. I consider her a friend. So as a friend, and not as a bodyguard, if you do anything to hurt her, I will personally make sure you never have the ability to hurt anyone again. Do I make myself clear?"

Oliver blinked at him and gave a short nod. "Yeah. Crystal."

"Good." He took a step back, stoic face back in place. "Enjoy your evening, Mr. Queen."

"Okay…" He stepped past him and toward the door before pausing and walking back. "Just to be clear... I understand that she's a friend and you're looking out for her, and you might not believe this at all, but… I've liked Felicity since I was fourteen years old. I've done numerous ridiculous things in an attempt to get her to notice me. I once sent her twelve bouquets of roses on Valentine's Day but chickened out on signing the card, and then found out she was allergic." He shrugged. "So I know you're trying to keep her safe, but I'm the last person you need to be worried about. This is the first time I think I might actually have a chance, so I'm not going to waste it."

Diggle stared down at him, eyes narrowed slightly. "Roses, huh?"

"She sneezed for three hours and eventually had to go home early. I haven't sent flowers to anyone since."

Amusement began to thread into his expression and Diggle nodded. "All right. I'll give you the benefit of the doubt." He raised an eyebrow. "Don't screw it up though. You only get one pass."

He grinned. "Good. Thank you."

With that, Oliver finally walked away, making his way outside to see Felicity standing near the bottom of the stairs, clutch in one hand and phone in the other.

He shrugged off his jacket as he walked down the stairs. "Gets cold at night," he told her, dropping his jacket over her shoulders.

She turned to face him, half-smiling. "I guess I didn't learn my lesson the first time."

He let out a chuckle, grinning. "You remember that."

She tipped her head, amused. "I remember a lot."

He winced. "How much is a lot?"

"I think the first time was when you put your hand in the punch bowl…" She hugged the jacket closed around her. "Sorry I left so abruptly, but if Taylor saw you, I think you would've been at the top of the gossip list before the dance ended."

His eyes widened a little. "You left to save me?" he asked, his brow furrowed.

She shrugged. "It was the least I could do. You looked pretty upset."

"Yeah, well… It was the first time I actually got your attention."

Felicity let out a surprised laugh. "Not the first time… I mean, that was the first time you actually tried to talk to me, but I noticed you before that."

"You did?" he asked hesitantly. "It wasn't when I tried to jump off the roof of my house, was it?"

"No, but that's definitely memorable..."

He shook his head, tucking his hands into the pockets of his pants. "Yeah, well, go big or go home."

"Or, in that case, the emergency room…" she said wryly.

"Wasn't the last time I made it there," he laughed.

"The first time I noticed you was in grade 8. It was English class and the teacher asked Tommy Merlyn about a book we were reading. He didn't have the answer and the teacher was kind of picking on him for it, but then you jumped in, distracted him." She looked up at him, smiling. "You got detention, but… you saved your friend. And, I don't know, it was admirable."

Oliver thought back to the time she was referring and nodded. "I remember that… Tommy's usually on top of his homework. He was a lot more of an academic than I was. But… That weekend was the anniversary of his mom's death and… He doesn't cope well, around then. So… He just needed a break."

Her face softened. "See? Admirable."

He grinned down at her, opening his mouth to say something only to turn as a cab pulled up to the curb. "Oh, uh, I had a bourbon earlier, so I hope you don't mind taking a cab."

"No, that's fine." She moved toward the door, but he reached it before her, pulling it open for her to climb inside. She smiled up at him before she ducked inside and took her seat, tucking her dress in and out of the way.

He closed the door before circling around to get in on the other side. As he sat down, he turned to her. "Do you know where you wanted to eat?"

"Uh, yeah…" She looked forward to the driver in the front. "Big Belly Burger? On fifth?" She glanced at Oliver. "Unless you were thinking of something else?"

He shook his head. "No, that sounds great."

Nodding, she sat back. "They make the most  _amazing_ burgers." She pressed a hand to her stomach. "And I don't know about you, but I haven't eaten since before I had to pull on this very unforgiving dress."

His gaze fell to the gown she was wearing, half covered in his suit jacket. "Can't say I've had the same issue."

She snorted. "Well, you're lucky. All the take-out I eat is a lot more noticeable when I'm wearing figure-hugging dresses. If I could get away with wearing a suit to these things, I would."

Oliver briefly found his mind wandering to Felicity in a power suit. She'd always been partial to dresses and skirts in high school. Much as she lamented her current dress, he couldn't say he was complaining in the least.

"I think you look stunning," he offered sincerely.

She ducked her head, reaching up to tuck a free curl behind her ear. "You don't look too shabby yourself." Her gaze fell to the suspenders he wore as she bit her lip. When they passed a street lamp, he noticed her cheeks were a little flushed and a stab of pride hit him hard.

Big Belly Burger looked just as it sounded; a little diner that they were probably very overdressed for. But Felicity didn't pause as she climbed from the cab, opening her clutch to pay for it. He tossed a fifty to the driver before she could and held a hand out toward the diner. "Hungry?"

She pursed her lips like she wanted to argue him paying for the cab, but curbed it and instead walked toward the diner, opening the door before he could get a chance to and pushing it open behind her for him to follow. Making her way to a booth, she slid in on one side and plucked two menus up from behind the napkin dispenser, placing one on the other side for him. He took a seat across from her and looked over the menu, his attention divided between her and the food.

She was tapping her mouth absently, brow furrowed in concentration as she read through the burgers.

"Girl, who do you think you're fooling? You get the same thing every time," an amused voice told her.

Felicity looked up with a grin at the older waitress sidling over to their table, a coffee pot in one hand while the other rested on her hip. "Double cheese burger with extra pickles, fries with a side of gravy, and a vanilla milkshake," she said knowingly.

"You know, I might change my mind one day, and then where will you be?" Felicity returned.

"In cardiac arrest," the waitress snarked. Her eyes cut to the right and spotted him. "Who's the guy?"

"Oh, this is Oliver. We went to high school together," she said, waving a hand toward him. "Oliver, this is Jackie. She's worked here almost as long as it's been open."

"Yeah, and I would've been out of here already too, if someone didn't let her guard off duty early, giving Carly a reason to beg me to stick around."

Felicity offered an apologetic smile. "Well, on the bright side, Carly and Digg get some time alone."

"Yeah, and it looks like she's not the only one with a good looking man to keep her company." She raised an eyebrow at Oliver. "You know what you want, honey?"

"Oh, uh…" He glanced down at the menu. "I'll just have what she's having. Except a coffee instead of a shake, please."

"You got it." She reached down to turn over the coffee mug in front of him and filled it up before sashaying away, sneakers squeaking on the floor.

"She's a character…" Oliver mused.

"Of the best variety," Felicity agreed. Resting her elbows on the table, she stacked her hands for her chin to rest on. "So, tell me what you've been up to. I've noticed a distinct lack of 'Oliver Queen' in the tabloids…" She raised an eyebrow. "If I remember correctly, you were voted 'Most Likely to be a Tabloid Favorite,' but I haven't heard a peep from TMZ…"

He shrugged. "I got some good advice in high school that I should do something that was right for me instead of something other people expected of me… Took a little while for it to sink in, but after I dropped out of the first two schools, I realized I was chasing the wrong person's dreams." He cleared his throat, leaning forward to rest his elbows on the table. "So I opened my own club. My dad wasn't exactly… proud of my decision, but he came around. Turns out I have a good head for the club business, at least. I've turned it into a chain. We have six right now all up the west coast, and we're planning on expanding soon."

"Six." She grinned at him. "That's amazing."

He ducked his head a little as he smiled. "Yeah. Turned out to be the best decision I ever made."

Reaching across the table, she found his forearm and squeezed. "Good for you."

He stared down at her hand, his heart stuttering in his chest just like it did when he was younger. "What, uh, what about you? You're CEO of Smoak Industries now?"

She nodded. "Yeah. Well…" She rolled her eyes. "My dad was eager to quit, but we talked him into holding on a while. I was in MIT for four years, and then, when dad started talking about retiring, I went back to school for a business degree. Then I spent about two years shadowing him, learning the ins and outs. And a year ago he officially retired and put me in as CEO." She shrugged. "It wasn't exactly what I was planning to go into, but I can't say I don't enjoy it. We're primarily a tech company and since I run it, I get final say on anything we're doing. If I want to jump in and get my hands dirty, it's not like there's anyone to stop me."

"So you like it? You're happy?"

She nodded. "I am. And I'm glad my dad isn't stuck in a job he doesn't enjoy. He was miserable, especially since my mom passed away. She kind of took that last bit of joy along with her and I think having this job on top of everything was draining him."

"Yeah… yeah, my dad died about five years ago. It was hard on my mom at first, but she's bounced back. She's got Walter now and she's a lot happier than she was."

"I heard." She shook her head, her face full of empathy. "They said it was a heart attack?"

"Stress induced." He nodded, clearing his throat when it clogged with emotion. "He, uh… He spent a lot of time at work, didn't have much time for anything else, and I guess it got to him."

"It can be stressful, having all those people depend on you," she agreed, nodding.

He stared at her then, searching her face. "So what do you do to relieve the stress?"

"Well, I start by taking handsome men out for burgers," she said, her lips curling in a grin. "We reminisce about high school and the good ol' days, and then I seduce him with my wealth of pop culture trivia and dorky but somehow endearing habit of babbling when I'm nervous. Something I've sadly not grown out of despite eight years of college and a life time of etiquette classes."

"Seduce, huh?" He arched an eyebrow. "Is that a promise?"

She grinned at him, her head falling back as she let out a sweet laugh. "You're a lot smoother than I remember."

He laughed. "In my defense, that only happened with you."

"Should I be flattered?" She tipped her head, grinning at him.

He mimicked the pose. "You should."

Smile softening, she let her gaze fall for a moment. "Then I am."

A milkshake slid into view then and she brightened, offering a thank you up to Jackie, who winked down at her, wiggled her eyebrows in Oliver's direction, and walked off to see another table.

"Excuse her lack of subtlety. She gave up on being discreet years ago," Felicity muttered, shaking her head before she wrapped her lips around the straw to her milkshake.

"You bring a lot of men to Big Belly Burger?" he teased.

"Only the good looking ones I have history with," she replied cheerfully, plucking the maraschino cherry from the top of her milkshake and tucking it between her teeth. She scrunched up her nose as she pulled the stem off to absently tie into a knot.

"You have a lot of guys from high school looking you up…?"

She shrugged, turning her eyes up thoughtfully. "Well, after MIT, Taylor and I tried dating again."

"Yeah?" He reached for a pack of sugar and shook it out before pouring it into his coffee. "Any passion?"

"Passionless," she lamented with a frown. "Which seems weird for a man that good looking… My friend Kelsey thought it was me. She was pretty sure I had a libido deficiency, but I think it was a mutual issue. He admitted later that he was just comfortable with me. We made sense on paper but not so much in bed, if that makes any sense."

He nodded. "I can't say I've ever had a problem in bed, but I understand the theory."

She chuckled. "No, I seem to remember you were pretty happy jumping from bed to bed in high school. Not a stranger to passion."

"More passionate with some…" He eyed her thoughtfully. "Anyone else look you up?"

She hummed. "Well, I ran into Carter Bowen a few weeks ago. Apparently he's writing a book on… something I can't wrap my tongue around, let alone my brain."

"Not a big fan?"

She pursed her lips in a frown. "Not so much. It isn't that he's writing a book, because good for him, it's the way he talks about it. I don't like it when people pretend to be something they aren't. He's smart and charming, good for him, he should own it. But there's a difference between being proud of your accomplishments and pretending like you're surprised when you've achieved something. You don't need to rub that in people's faces, especially not in an effort to make them look bad." Her eyes narrowed. "He's like a sneaky bully, sliding in under the radar and making people feel like crap, but doing it in a way that makes you look bad if you call him out on it."

"Sounds like you've got some pent up aggression toward Carter."

She tossed him a lighthearted glare. "Just him and people like him."

"So I should own up to my accomplishments, but not too much?"

"Yes." She nodded. "I said be proud, not rub it in my face that you're better than others."

"Well, he could be the next Dr. Oz, Felicity. We should probably give him props."

"I am  _not_ watching that show," she told him, shaking her head. "I don't care if he comes up with the cure for cancer… Okay, maybe I care if he comes up with the cure for cancer. I had an aunt who had cancer. It was awful. She died. Not from the cancer, but it definitely didn't help."

His mouth twitched. "I'm seeing the endearing side of that rambling thing."

She bit her lip to hide her smile. "Well, that's a positive. Usually I just stick my foot in my mouth and hope people didn't notice." She shook her head, laughing at herself. "I had a business meeting with an investor last week and I kind of implied I'd do anything for him to keep investing in the company, and then I realized my faux pas and tried to fix it by insulting him by saying I'd  _never_ sleep with him…"

He let out a gruff laugh. "I'm sure he appreciated that."

"He understood what I meant and forgave me, but I still think about it and cringe."

"Not enough passion for you?"

"Shut up," she muttered. "He's older than my father. Not that there's anything wrong with older men. They have a certain appeal. But I wasn't interested and he wasn't really my type."

"You have a type?"

She looked up at him, eyebrow raised. "Didn't we establish that I like handsome men I knew in high school?"

"Yes, but you've been pretty finicky so far. Both Jeffries and Bowen are knocked off the list."

"Which only boosts your chances," she added, before casting her eyes toward Jackie, who was walking toward them with a tray full of food.

The topic was dropped momentarily as thick cheese burgers, fries, and a large side of gravy to share was placed between them. "Enjoy!" Jackie said before walking off.

Felicity happily plucked up the slices of pickle on the side of her plate and chewed on one while she cut her burger in half with the extra knife Jackie had dropped off.

Dressed in a stunning evening gown, she wasn't the least bit self-conscious as she took a large bite of her burger, catching the juice that dribbled down her hand and licking it off. She gave a little laugh and reached for a few napkins to dab at her chin, before raising an eyebrow at him. "Good?" she wondered.

Distracted watching her, he only just then picked up his burger for a bite. His eyes went wide as the flavors of spices and meat filled his mouth and gave an appreciative moan as he nodded. "Really good," he told her.

She grinned as if she'd made it herself. "Best burger joint in Starling, hands down," she claimed before grabbing up a fry and popping it in her mouth. "So, tell me about your family. Is Thea your only sibling?" she wondered.

He nodded. "Yeah, my parents didn't have her until I was ten, so I was used to being an only child and getting whatever I wanted."

Her mouth twitched. "Did you resent her a little when she came along then?"

"Just the first couple years. Then she was old enough to chase me everywhere and I kind of liked being her favorite person." He shrugged, reaching for the ketchup and spraying a gob onto his plate to dip his fries in. "I still do… What about you? Any siblings?"

She shook her head negatively. "No. My mom always wanted more kids but it just wasn't in the cards for them. My dad used to say I talked enough for three kids anyway… I always wanted a little brother or sister though. I guess my friends kind of filled those slots."

"Yeah, you were friends with Kelsey Daniel's in high school, weren't you?"

"Mm-hmm. Kelsey Daniels, Anna Cochran, and Illena Walker. Kelsey's still as wild as ever. Anna married her girlfriend last year and they just adopted a little boy, who I fondly refer to as my nephew as often I can. And Illena is traveling in Europe. She never really likes to stay anywhere for too long." Her brow furrowed. "I only really remember you hanging out with Tommy Merlyn."

He shrugged. "There were others, but Tommy was the constant."

"He was there tonight, wasn't he? So you two must still be close?"

He smiled. "He manages my club, actually. He was still in college when I opened the first one, but when he was finished, he wanted a change of pace. I don't think he really wanted to follow his dad either. So I asked him if he wanted to manage Verdant and he jumped on it."

"Verdant, huh?" Her gaze fell to the green silk tie he wore, currently tossed over his shoulder while he ate.

"Green's my favorite color."

"Looks good on you," she murmured before focusing back on her burger.

He smiled to himself.

Dinner passed easily, taking a little longer in between conversation. He told her more about Thea, who she was when she was younger and what an amazing young woman she'd grown up into. Their father's death had hit her hard, but he thought the experience brought them together more. It'd been difficult to get used to her growing up at first, still used to the enigmatic little girl who used to chase him everywhere he went. But she'd become independent and grew out of her idolization of him, kicking him off his pedestal and appreciating him for who he really was. She was planning on going into fashion when she finished high school, and was already looking into design schools in France. The pride was obvious in his voice; he loved his sister and, while their mother lamented that neither of her children wanted to take over Queen Industries, she and Walter were handling that for now.

"Was it weird? Having Walter become part of the family?" she wondered.

The plates were cleared and she'd traded in her empty milkshake cup for a mug of tea.

"At first, yeah. But, to be honest…" He shook his head. "I don't think my mom was happy with my dad. And it was mutual. I think they stayed together because it was familiar and they felt they owed it to me and Thea. My dad wasn't the most… faithful man, and I think that weighed on my mom. But now she has Walter and he's devoted to her, like she deserves."

Felicity stared up at him, letting his words sink in without comment.

It felt good to talk about it. He didn't discuss his parents very often. Their issues, their fighting, had bothered him growing up, but he chalked it up to being married as long as they were. They were bound to disagree. As the years went on, those fights increased and it became clear it wasn't just about time management. His father had a number of affairs and while he didn't rub it in Moira's face, she was well aware. Later, after he'd died, Oliver had wondered if he might've followed in the same footsteps as his father. If he hadn't taken another path, if he'd done what was expected of him, would he be the CEO now? Maybe he would have married Laurel like she'd once expected, early in their relationship. They'd have children and grow older and he'd sleep with his EA or whatever pretty face passed him by. But she would forgive him or learn to ignore it and so he'd go on making mistake after mistake, leaving them both angry and miserable. Until one day he had a heart attack at his desk, his face in his lunch, his hand clutching his chest, the last memory of a great man being that he worked too hard and it was never worth it.

"Are you okay?"

He focused suddenly, finding Felicity watching him carefully.

"Heavy topic," she murmured. "It's not hard to let it swamp you."

"Yeah, no, I just… I guess I was wondering what life might be like if things were different."

"Ah, the 'what if' game…" She nodded. "I've played it a few times."

"Yeah?"

"Sure." She shrugged. "What if my dad wasn't a CEO? What if I grew up in a middle class family in some small town? Would I have still gone to MIT or work in tech? What if my dad loved his job and didn't want me to take over for him? Would I be working low on the totem pole at SI or would I have applied somewhere else? Like Wayne Industries; they have an amazing applied sciences program." Her brows hiked. "Or the obvious, what if I stayed with Taylor? Would I be a married mom of two brilliant kids who loved bad jokes and too much tweed?" Her nose wrinkled and he let out a laugh.

"What if I didn't put my hand in the punch bowl at the winter formal and actually managed to ask you out?"

She smiled softly. "What if I said yes and we spent the whole night dancing?"

"What if I asked you to be my girlfriend?"

"What if we spent the next year and a half together before I left for MIT?"

"What if we had a long distance relationship that actually worked? And I visited on weekends and you came back for holidays…"

"And I got to see Verdant grow from the ground up, cut the ribbon, watch you become the club owner you are today…"

He nodded. "You might still be a married mom."

"But no tweed, so that's an upside."

He grinned, licking his lips.

Felicity shook her head. "My mom used to say that 'what if's' are for people who aren't happy with how their life turned out, but focusing on all the different paths it could have taken means you miss the ones it could still take…"

"Is this where you seduce me?" he asked, leaning forward in his seat.

"I've been doing that since I found a way to run into you tonight. This is me telling you that I don't know where this road leads, but I've enjoyed talking to you and I'd like to do it again. Preferably over breakfast, in my apartment, without any pants on."

Nodding, he dropped his gaze to her mouth. "Shouldn't we test our passion out? Might not be compatible…"

She rolled her eyes and slid out the side of the booth, passing him his jacket before she smoothed out her dress. "You can kiss me while we wait on the cab. If it sucks, we go our separate ways and you can bury the torch you've been carrying. If it doesn't, you get to knock a 'what if' off your list. I don't see a downside here." She pointed at him. "While you think about that, I'm going to get the bill."

He opened his mouth to argue that he should pay, but she arched an eyebrow back at him and he raised a hand in surrender. Apparently this was going to be 50/50 from the word go.

Oliver pulled his coat on as he thought about her offer. It wasn't a long-term definite, but she did offer breakfast, which meant she didn't plan on kicking him out right away. At least, not if he didn't disappoint. Taking the chance, it wasn't like he'd ever get another one, he stood from the booth and moved to join her. She'd paid the bill and was outside, just hanging up her cell phone when he stepped up behind her.

She turned to meet him. "So? What's the verdi—?"

He cut her off with his mouth, slanting his lips over hers with all the pent up emotion of fourteen years. Sure, some of that he'd spent growing up and moving on from his crush, but as soon as he set eyes on her again, it had rushed back to him tenfold. There was a reason that sweet, geeky, insanely smart and equally pretty Felicity Smoak had been the exception in high school and there still was now. Any fear that there wouldn't be passion between them was quashed right then and there. His fingers sunk into her hair, holding her head steady as he suckled her bottom lip, dragging his teeth over it. His hand at her waist squeezed lightly before sliding up the slope of her back. Her arms wrapped around his neck, one hand dragging down his neck while the other gripped his shoulder tightly, balling up the fabric of his jacket in her palm.

When he broke from her lips, he was panting, and made quick work of kissing down her jaw to her neck, suckling and nipping at her skin. He could smell the perfume she'd dabbed there; light and floral. God, she was soft, her skin like satin under his lips.

"It's my lotion," she said, her voice a little hoarse.

Apparently he was talking out loud…

She chuckled lightly. "It's cute. Usually I'm the one saying whatever's on my mind."

He kissed her chin and tipped her head back up to meet her eyes. "I'm probably going to embarrass myself in front of you a lot, try not to hold it against me."

Smiling, she rested both hands on his shoulders. "I don't think you can do much worse than throwing up on me."

Groaning, his head fell back, but her lighthearted laughter somehow made it seem much less awful. What was even better was her reaching up on her tip toes and kissing down the length of his neck, scraping her teeth over his Adam's apple and nipping at his collar bones.

When the cab finally pulled up, he was slightly disgruntled that they had to pull apart, enjoying the way her hands had slid under her jacket to stroke up and down his chest. But then they were climbing inside and on the way to her apartment, so complaining seemed a moot point.

Oliver could honestly say that he had made out in a lot of cabs on the way to someone else's place for a nightcap. But there was an intensity that hung in the air as he had Felicity pressed up to his side, her head leaned back against the seat as she looked up at him. His arm was around her, fingers lightly drawing circles down the length of her bare arm. She caught his chin, her thumb pressed to it and her fingers scrubbing the underside of his jaw, nails teasing over the scruff there. He leaned toward her, his nose brushing against hers, but didn't reach for the kiss he wanted, instead staring into her eyes, a deep, cobalt blue. He remembered being seventeen and wanting to count the freckles on her nose. He kissed the tip and then the bridge and up between her brows before lingering at the corner of her eye and dragging his mouth down the apple of her cheek. His lips smoothed over the line of her jaw, kissing the corner of her mouth, and then the other, before finally resting just a hair's breadth from her mouth.

Her hand slinked around to the nape of his neck, lightly grazing her nails back and forth. He cupped her face as he kissed her, thumb gently brushing as his tongue ran the seam of her lips. She opened on a sigh and his tongue mapped out the roof of her mouth, flicking the back of her teeth before he nipped at her top lip and soothed it away with a sipping kiss. He kissed down her chin, ducking to her neck and suckling kisses along her soft, soft skin. He dragged a hand down the lace overlay that covered her up chest, his thumb following the aquamarine line down the center of her dress to her stomach. His knuckles briefly rested in her lap before he slid his hand to her hip, squeezed, dragging it down her leg.

The cab pulled up in front of a tall building and they hurried out, paying quickly before they made their way up the stairs. His arm wound around her waist as she dug in her clutch for her keys and unlocked the front door. She waved at the front desk security as they passed, making their way toward one of the two elevators across the marble floor of the front entrance.

As soon as they were inside and she'd pushed the button for the penthouse, she had him pinned to the wall. His tie was pulled loose as she made quick work of the buttons on his shirt. Reaching up to kiss him, she pressed tight to his frame, her hands gripping his suspenders and dragging down, knuckles rubbing against his skin. He hummed, skimming his hands up her back until they reached the top of her dress and found the zipper. He pulled it down quickly, his hands parting the fabric to touch the soft expanse of her back, no straps telling him there was no bra to be found. He growled, kissing her a little harder, turning her so she was pressed to the wall, his hips tight against her own.

When the elevator dinged, they hardly parted. He pulled her off the wall, arm still around her and walked her down the hall to the only door on the top floor. While she turned to stick the key in the lock, he stood behind her, hands sliding under the fabric and around to her front, skimming up her body until he had her breasts cupped in either palm.

She let out a breathless noise and arched into his touch, the key losing direction and scraping the door as his thumbs thrummed her nipples. He nuzzled under her hair and kissed down her neck, nibbling at her nape and pressing sucking kisses across one bared shoulder blade.

Focusing, she got the key in the lock and turned it, shoving her door open and reaching around for the light switch.

They stumbled into the apartment with him kicking the door closed behind them. Felicity pulled the sleeves of her dress down her arms and let the fabric hang from her waist. He mouthed across her shoulder as he looked down at his hands, wrapped snugly around her breasts. She covered his hands, directing his thumbs to move the way she liked, rubbing and flicking against her nipples. She leaned into him, pressing her ass up into the cradle of his hips, rubbing against the bulge of his erection.

She enjoyed herself for a few minutes before turning in his arms, his hands falling away. She shoved his jacket off, leaving it on the floor, and reached for the cuffs of his shirt to undo them. His shirt followed his jacket, but she left the suspenders in place, her eyes flashing dark with desire as she tugged on one. She kicked her heels off, a tall set of purple pumps that dropped her down a good five inches as soon as they were gone. He wrapped an arm around her and lifted her up, wrapping his mouth around a pebbled, pink nipple, teasing it with his teeth and tongue. She skimmed her fingers back through his hair before hugging his head to her, arching up into the suction and seduction of his mouth.

"Bedroom?" he asked.

"Straight ahead," she murmured.

He started walking, carrying her easily, and smiled as she reached out to use the wall as a kind of steering wheel, pushing them left to avoid a table and then right when he nearly knocked over a plant of some kind. Finally, they were at her bedroom, double glass doors already opened, white fabric draped in them. He briefly remembered the winter formal and how beautiful she'd looked in white, and then he was focused back on the present with her in front of him.

He let her down and watched her reach behind to drag the zipper of her dress down a few more inches before she shimmied out of her dress, letting it fall in a pool around her feet.

He dragged a hand over his mouth and let out a shaky breath at the sight of her in black lace, a matching garter belt around her waist, reaching for the sheer black stockings that hugged her legs, sitting high on her thighs. Oliver dropped to his knees in front of her, dragging a hand up the backs of her legs, from her ankles to the top of her stockings, tracing the edge with his fingertips. He kissed the top of her thigh, dragging his teeth up along where the satin strap reached from stocking to garter belt, his nose brushing against her lace underwear and he mouthed his way across the front, sliding his hands around to the back of her thighs, parting them further. He kissed the inside of her thigh, tangling his fingers in the straps for a moment. He looked up at her, staring down at him, his mouth traveling higher, resting against the damp lace that covered her. He flicked his tongue over it, getting just a faint taste for her. He wanted more. He reached up and drew the fabric to the side, letting his tongue drag across her wet slit.

She gripped his hair tight between her fingers, her head falling back. Burying his mouth against her pussy, he slid his hands up to her ass and pulled her in tight, his tongue teasing her apart, lips suckling at her like a man searching for water in a dessert. She ground herself down on his mouth, whimpering as his tongue swirled around her clit.

The edge of her underwear was chafing the side of his mouth, or that's the excuse he was ready to give when he tore off the edges and threw the useless scrap of lace out of the way. He hooked one of her thighs over his shoulder, spreading her open further, and sunk a finger inside her, pumping slow and measured. Felicity was watching him from hooded eyes, biting her lip as she rocked against his mouth and back onto his finger. She was gorgeous; a flush riding high on her chest and burning her cheeks. That innocence he'd once found so fascinating about her in school was replaced with the seductive femininity of her taking pleasure from him. She reached up to untie her hair, letting it fall in a riot of curls around her shoulders. He had so many fantasies that looked just like this…

He sunk a second finger inside her, curling it and moving it a little deeper, a little faster, while he licked her leisurely. He could do this all night. He could lay her back on her bed and just eat her out until the sun came up. And then for breakfast, he'd fuck her on her kitchen table until she screamed his name so loudly it'd be the most familiar word her tongue had ever known.

He stood then, dragging his mouth from her to press sloppy kisses up her stomach. He hooked an arm around her legs and lifted her, walking them to her bed, a queen with a wrought iron head board of interlocking bars he was going to have her hold onto later. He laid her back on the bed while he shucked his pants, losing the suspenders on the way. She pouted as they left his shoulders and he filed it away for another time.

He crawled onto the bed and laid back before reaching for her. "Come here." He maneuvered her so she was bent over his face, his mouth between her legs. She leaned back, her hands braced behind her on his stomach. His hands found her ass and pulled her forward, meeting the downward stroke of his tongue sliding between her slit. He could feel her nails bite down against his stomach and her thighs shaking on either side of his head, but it only made him smile, sucking her folds between his teeth and letting them drag over the sensitive skin. She bucked against him, letting out a cracked whimper. He kept her like that, right on the edge, teasing her until she was rocking her hips desperately, her head falling back, hair dragging against his stomach.

"Oliver," she said, breathless and needy.

He was going to do this again later. He was going to wake her up like this, he decided. But right now, she wanted more and he needed to be inside her.

He focused on her clit, sinking two fingers inside her while his other hand slid up her body to curl around her breast, plucking and rubbing her nipple. It didn't take her long to tip over the precipice, letting out a huffing breath and murmuring his name, over and over, as wave after wave made her shake, her thighs slick with her pleasure. He slid her back, settling her on his stomach as she came down, still enjoying the feeling coursing through her.

He unsnapped the straps from her stockings and slowly rolled the sheer fabric down her legs, sliding it off and tossing it away while his fingers kneaded her calves.

She smiled down at him, flushed and satisfied, her grin warm with fuzzy affection. She ducked down for a kiss, taking her time on his mouth while her body slid down to lay against his, all soft curves and bare skin. He dragged his hands up and down her back, enjoying the feel of her, fitting against him perfectly. He brushed her hair off her back and traced his fingers from one shoulder to the other, drawing random shapes in the middle. Her kisses were lazy, tugging and sipping at his lips, flicking her tongue over them and dragging it along his tongue.

He could see himself doing this for a long time. He could see this passion simmering for longer than any of his previous relationships. Fourteen years he'd wanted her and the payoff felt amazing so far. He didn't want this to stop. He didn't want to go back to how it was before. All business and very little play. But he also didn't want it to turn out like the last few tries at relationships had. He should have pushed for a few dates before the night cap, but he couldn't say he was exactly disappointed. He'd just have to make it worth it, convince her to spend more than just a night with him. Sex was all good and fun, but he wanted more. He wanted to know everything that made her tick. He wanted her to share her good days and her bad days with him. He wanted to rub her feet after a long day at the office and kiss her before he left for the club. They weren't 'what if's,' not exactly; they were the roads of opportunity just waiting to explored.

Felicity leaned over to the bedside table to grab out a condom before she sat back. He reached past her to shove his boxer-briefs down off his hips and she twisted to help him get them off. She slid back onto his thigh and dropped the condom to his stomach before she tucked her hair behind her ears and leaned down. With little warning, she slid her mouth over the head of his cock, flicking her tongue over the pre-cum beaded there. She sunk her mouth down further, licking the underside before she raised her head, replacing her mouth with her hands. Felicity liked giving head as much as she enjoyed receiving it. She watched him, a glint in her eyes as she licked his tip before pressing sucking kisses down his shaft and along the V leading down from his hips. She nipped at his skin, scraping her teeth against him and flicking her tongue out to soothe the sting, all the while leaving her hands to continue working him, twisting and pumping him until he was so hard it was almost painful. And then her mouth was on him again, taking him deep inside, her cheeks hollowed out. He could hardly see her with all that hair falling as a cover, but the sensation had his eyes rolling back in his head half the time anyway.

Panting, he reached for her, his hands squeezing her shoulders, and she let up, reaching for the condom. He needed a minute to recover before he could handle her touching though and took her hands in his, braiding their fingers together and pulling her forward. She leaned over him, dropping her mouth down for a kiss.

A few minutes passed before she laughed lightly against his lips.

"What?"

She shook her head. "Fourteen years to gather up the courage. If I knew you were this good, I would've said yes the first time you tried to talk to me."

He grinned. "You were intimidating."

She scoffed. "I was not. You were just used to girls falling at your feet."

"True," he admitted, reaching up to brush some of her hair back from her face. "But I never liked anyone the way I did you."

"No?" She stared down at him curiously. "And what was it about me that got you wound up?"

"I used to hear you talking to your friends. You were a few lockers down from me. And you used to go off on these little tangents about things; school or your dad or whatever. And I always thought they were the cutest thing…"

She groaned. "Having no filter is not cute."

"It  _is…_ You were funny and sweet and… so pretty." He pressed a kiss to the tip of her nose. "I can't count how many times I psyched myself up to talk to you and chickened out…" He snorted. "Not that my record of actually talking to you turned out all that well."

"I don't know. That last conversation was pretty memorable," she argued. "I held onto that jacket for years. I wore it all through MIT, but I lost it somewhere in the move back here."

"You wore it to school a couple times, too," he remembered. Three times actually. He stared at her for five minutes straight the first time he saw her walk into the school with it on. The following two times made sure he never stopped smiling for the rest of the day.

"It was comfortable."

"It was huge on you."

"I like big things." She smirked, wiggling her hips back against him.

He grunted, reaching down and squeezing her thigh. "Condom," he gritted out.

With a playful salute, she sat back and balanced on his thigh as she rolled the condom down his shaft.

He was about to fuck Felicity Smoak.

There weren't enough fingers to count how many times he'd dreamt of this. The reality was so much better. She sunk down on him, her mouth falling open on a sigh, and nails digging into his chest. He pressed up into her, heels sunk down on the mattress, and let out a shaky sigh. Fuck, she felt good. She rocked her hips forward and around and raised herself up off him. His hands skimmed up her thighs, fingers tangling in the lace belt still around her waist. She pressed her palms flat against his chest as she rode him, bouncing quick and hard against his lap. He watched her face, twisted in pleasure.

Now that was beautiful. She arched her body back, shoving her hair over her shoulder, and slid a hand down to cup her breast, squeezing and kneading it, rubbing her nipple in tandem with his thrusts inside her. She moved fluidly on top of him, grinding down and seeking out her pleasure without apology. She slid a hand between her legs to stroke her clit the closer she got, biting down hard on her lip, her brow furrowed with concentration, and it was the sexiest thing he'd ever seen.

When she came, he had to twist his hands in the blanket beneath him, gritting his teeth as she slowed her hips down, fluttering all around his shaft. Sweat shone on her skin, the tension bleeding from her body. He rolled her over onto her back, still hard and thick inside her, and licked a droplet of sweat that dipped into her collarbone. He kissed up her neck, leaving bruising kisses everywhere he reached. Her legs hugged around his waist, crossed at the ankles over his back. He slid his hands under her back and lifted her up as his lips traveled down her chest, mouthing kisses over the tops of her breasts and tugging at her nipples. She squirmed under him, both arching up to meet his lips and pulling away from the sting of his teeth. He swirled his tongue around them before dragging his face down the valley of her breasts, kissing across her ribs before he made his way back up.

"I wanna take my time with you," he told her, sucking on the ball of her shoulder.

"After," she panted. "All night, all morning." She squeezed her legs around him and clenched around his cock. "But I think you need a little relief to tide you over."

He grunted, pressing his face against her neck and licking his way up behind her ear. He tugged on the woven gold hoop earring there and nuzzled up around the shell of her ear.

Felicity's hands slid up his back, fanning out over her shoulders, and dug her nails in. "This is a good time to prove that passion isn't fleeting," she told him.

He grinned, kissing down her cheek to her lips. She let out quick, sharp breath as he thrust into her, the bed shaking beneath them. Oliver braced his knees and elbows down on the mattress as he pulled out slowly, teasingly, and then he nipped her bottom lip as he sunk back into her to the hilt. She stared up at him, meeting his eyes as he continued the same pattern; slow as he left and fast as he returned. He reached down for one of her legs and bent it back, swiveling his hips as he pulled out. He hooked her knee over his shoulder and slid a hand between them, his thumb rubbing circles around her clit.

He fucked her like that until the build-up was almost too much to take. He licked the sweat from her skin, their bodies sliding together easily, fitting like puzzle pieces finding their home. He kissed her parted lips and down her neck, across her shoulders, and the palms of her hands as he raised them up to meet his mouth. He kissed her fingertips and her wrists and felt the hard beating of her heart wildly thrumming under his grip as he pinned her hands above her head.

When he finally came, he had his forehead pressed to hers, her name grunted from gritted teeth. She was squeezing all around him, her own climax ebbing away slowly. Every muscle uncoiled until he was just limp, resting on top of her, his head on her shoulder. She stroked her fingers down his neck lightly, curling them in his damp hair.

It took him a minute before he could stand, his knees shaking as he discarded the condom in a waste basket. She laid sprawled on the bed for a few more minutes before finally crawling off of it and walking toward a door leading into her en suite. "Shower?" she asked him, already digging towels out of a linen closet.

He followed after her, his legs beginning to find their balance once more.

Their shower was quick, but playful. Felicity scrubbed him down with her mango body wash and he took it upon himself to wash her hair. He could admit to being slightly fascinated with all those curls. When they climbed out, he toweled her down and used it to pull her closer so he could steal a kiss. She arched up, arms wrapped around his neck, and met his slanting mouth kiss for lingering kiss. Making their way back into her bedroom, she didn't bother with clothes, simply throwing her blanket and sheet back and climbing in. She braided her damp hair and shuffled down the bed while he climbed in on the other side.

It was intimate and oddly comfortably for him to tug her over to lay against him, her head on his chest as he tucked an arm behind his head. He still planned to make her grip the head board while he buried his head between her legs, but he'd give it a little while for them to recoup. Stroking his fingers back through her hair, he relaxed, sinking into the warmth around him.

"What're you doing tomorrow?" she wondered.

"Most of it'll be spent eating.  _You_. Breakfast, lunch, and dinner. Sun up to sun down."

"Talented tongue."

He grinned tiredly.

"Not sure sexual favors is all you have to work with. I wouldn't mind going out for dinner. We can see a movie later, something with lots of unnecessary violence."

His eyes opened, brows hiked. "Yeah?" he asked, wondering if he sounded as hopeful as he felt.

"Yeah." She turned her head to press a kiss against his chest. "Unless you've realized your crush was misguided and want to keep this strictly physical. Which, in that case, I'm good with just breakfast… Might as well take one for the road."

He laughed, his head falling back. "I plan on sticking around as long as you'll have me. I'm good with dinner and a movie."

"Great." Her fingers drew random patterns on his chest. "So, that's one 'what if' down, what do you think?"

He looked down at her, smiling. "It was worth the wait, but I don't plan on wasting another 14 years…"

"Good." She stretched a leg over him. "I can be really impatient."

Chucking lowly, he dipped down to kiss her, lingering against her lips, only breaking apart when she yawned, offering an apologetic shrug.

They fell asleep soon after, but Oliver held true to his plan. He woke her up with his head buried between her thighs, just as he planned to do for a long time to come.

The rest of the world tried to intercede midway through breakfast with a call from Tommy wanting details. He promised to tell him all about it when their date actually ended before hanging up and putting his phone on vibrate.

He wasn't sure that first date ever really ended though. They were basically inseparable as soon as they got together. They spent the weekend holed up in her apartment and when they had to separate for work, they were quick to find each other as soon as it ended. While passion might have been difficult between her and Taylor Jeffries, she and Oliver didn't have that problem. In fact, they had an abundance of it. Which is why he wasn't surprised when, three years later, they welcomed a daughter into the world.

Adelaide Queen, fondly referred to as 'Lady' by her Aunt Thea and Uncle Tommy, greeted the world early on a Sunday morning. Oliver fell in love with her much like he had with his wife; on sight. He married Felicity two years after reuniting with her and it was one of the best decisions of his life. His mother took the credit for bringing them together and proudly told anybody who would listen that she'd known since he was 14 that Felicity Smoak would be a life changer for him. She wasn't completely wrong, even if it did take entirely too long for him to finally get his chance with her.

All things considered, he was pretty sure his high school crush turned out a lot better than most.

{ **end**.}

**Author's Note:**

> As per usual, this was going to be something short and sweet and turned into a mini-monster. I considered breaking this up into two or three parts for easier reading, but there isn't really a good point throughout the flow to do that, plus a lot of readers tell me to just post the long chapters, so I hope this isn't too difficult to get through.
> 
> I hope you guys enjoyed this. It was fun writing Oliver as a lovesick teenager incapable of being as cool as he usually was around her. It was also fun writing his friends and family teasing him for that complete lack of cool. ;)
> 
> Please leave a review; they're my lifeblood. Especially when I spent as much time as I did on this sucker! Like, I wrote it all in one day and stayed up to 6am to make sure it was posted. So please, don't make me beg, review!
> 
> \- **Lee | Fina**


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